Ethanol → p-Toluenesulfonyl azide

HRID 2288566Notes

Reaction equation

HRID 2288566 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(O)C.[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>O>[C:14]1([CH3:15])[CH:16]=[CH:17][C:11]([S:8]([N:1]=[N+:2]=[N-:3])(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azideYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

71.5 g of sodium azide was dissolved in 200 mL of water and mixed with 400 mL of 90% ethanol in a 2 L Erlenmeyer flask. To this solution, 1 L of a 99% ethanol solution containing 190.5 g of tosyl chloride heated to 45° C., was added with stirring, and stirring was continued at room temperature for 2.5 hours. From the reaction mixture, ethanol was evaporated under reduced pressure, and to the residue, 1.2 L of water was added, whereupon an oily azide was separated by means of a separatory funnel, washed with water, dried by anhydrous sodium sulfate and subjected to aspiration filtration to obtain 160 g of colorless p-toluenesulfonyl azide.

Workup

  1. additionwas added
  2. stirringstirring
  3. customFrom the reaction mixture, ethanol was evaporated under reduced pressure
  4. additionto the residue, 1.2 L of water was added, whereupon an oily azide
  5. customwas separated by means of a separatory funnel
  6. washwashed with water
  7. dry with materialdried by anhydrous sodium sulfate
  8. filtrationsubjected to aspiration filtration

Sources & evidence

ORD record
ord-8bfa010d545d41d8a6b453a86f6b91c6
Source dataset
uspto-grants-2000_07
Patent number
US06090518

Reaction notes

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